Hydrochloric Acid → HCID 86717945, compound

HRID 2275874Notes

Reaction equation

HRID 2275874 reaction equation
Cl.C(OCC)C.[F:7][C:8]1[CH:46]=[CH:45][CH:44]=[C:43]([F:47])[C:9]=1[CH2:10][O:11][C:12]1[C:13]2[N:14]([C:18]([C:22]([NH:24][CH:25]([C:35]3[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=3)[CH2:26][NH:27]C(=O)OC(C)(C)C)=[O:23])=[C:19]([CH3:21])[N:20]=2)[CH:15]=[CH:16][CH:17]=1>>[NH2:27][CH2:26][CH:25]([NH:24][C:22]([C:18]1[N:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][CH2:10][C:9]3[C:43]([F:47])=[CH:44][CH:45]=[CH:46][C:8]=3[F:7])[C:13]2=[N:20][C:19]=1[CH3:21])=[O:23])[C:35]1[CH:40]=[CH:39][C:38]([F:41])=[C:37]([F:42])[CH:36]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86717894HCID 86717894, compound

Product 1

HCID 86717945HCID 86717945, compound

Procedure

3.1 ml of 2 M hydrochloric acid in diethyl ether (6.2 mmol) were added to 355 mg of rac-tert-butyl {2-[({8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridin-3-yl}carbonyl)amino]-2-(3,4-difluorophenyl)ethyl}carbamate (Example 77A, 0.62 mmol), and the mixture was stirred at RT for 5.5 h. The resulting precipitate was filtered off, washed with diethyl ether, suspended in dichloromethane and washed with saturated aqueous sodium bicarbonate solution. The organic phase was dried over sodium sulphate and filtered and the filtrate was concentrated and dried under high vacuum. This gave 279 mg of the title compound (94% of theory).

Workup

  1. filtrationThe resulting precipitate was filtered off
  2. washwashed with diethyl ether
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-97a3117dcbc54fa38c7d5a420fe8f34b
Source dataset
uspto-grants-2015_09
Patent number
US09126998B2

Reaction notes

Loading…